48 Questions That'll Make Awkward Small Talk So Much Easier

How many times per week do you find yourself participating in small talk about topics you have no interest in or have already discussed a million times—just for something to say? Whether it’s waiting for a really slow elevator with a co-worker, talking to an acquaintance at an industry event, or chatting with a complete stranger at a networking event, it happens to all of us.

So, to combat these incredibly boring conversations, I started asking people unexpected, thought-provoking questions that couldn’t be answered with a simple yes or no. The results were awesome: I learned cool facts about other people that I would’ve never picked up in “normal” conversation—and as a bonus we became closer. (And as a double-bonus, I got to stop weighing in on the weather.)

If you’re ready to start having awesome conversations, check out my list of favorite questions, divided by small talk topics that most people can get behind. Obviously these don’t apply to everyone in every situation—but there are certainly enough here that you should be able to avoid awkward silences for a long, long time.

Small Talk Questions 1-8
Work

If you weren’t working here, what would you probably be doing right now?

How did you become a [job title]?

What surprised you the most about your current job?

What’s the craziest thing a boss has ever asked you to do?

Would you rather work four 10-hour days or five eight-hour days?

If you were guaranteed to be successful, what job would you want?

What was your first job? Did you like it?

What’s the best career advice you’ve ever received? How about the worst?

Small Talk Questions 9-16
Entertainment

Are you reading any good books right now? I’d love some recommendations. How about shows?